5 Stages Of Image Mastery Part 3: A Well Dressed Man

It’s an eye opening moment in a man’s life to reach a goal he’s strived for, only to find himself thinking, “is that all there is?..”, “this is what all the fuss was about?..”

I found myself thinking these thoughts the first time I saw that I had clear abs in the mirror, or when after starting to offer personal consultations on SSfJ and found my services booked weeks in advance.

Sure, in both of those cases there was a moment of absolute joy and excitement (a bit less in the former than with the latter) but after that initial excitement passed – and it always does – I was in the same position as I was before:

I wasn’t much happier than I was before those events.

Women didn’t just start jumping on me the moment I left the house.

I was still confident in certain situations and uncertain, a little shy in others.

You see,

In every journey of personal development and improvement, after the initial spurt of results and improved self-image comes a point of plateau, where becoming better at the fundamentals no longer leads to a significant increase in the real-world results that we’re getting.

At this point we have three options on how we continue:

Declare that “it doesn’t work”, “doesn’t make a difference”, etc. and scrap everything to move onto the new shiny strategy – for example, after developing defined abs and realizing that women just don’t jump on you the moment you take your shirt off, you decide that it’s all a hoax, a marketing scam and get back to eating shit food and over the next few months put on weight while you’re contemplating if getting rich is “The Real Panty Dropper”

Decide that you’ve learned everything there is to know about the subject and while maintaining the good habits you’ve developed, you simply move on to learn and develop a new skill – let’s say you build a website that’s now generating a modest income, nice to have but not really a game changer. If you were to take this second path, instead of growing and improving your site, you would focus on building a new a site that uses different monetization strategies. You would keep your first site, but besides some maintenance to keep it generating that modest income, you’d more or less forget about it.

Change our thinking, double down and aim for mastery – realize that even though abs are nice to have, only when combined with a notable musculature, shoulders and chest will they lead to an awe-inspiring, show-stopping physique. In the same sense, having a site that generates some income is cool but it’s a completely different ball-game when you get to a point where it can support you fully and you can spend your days doing what you love and where you can make the biggest impact. To choose this path means that we need to change our thinking, explore different strategies than those that got us to this point because as the book title goes, “what got you here, won’t get you there.”

You might be wondering, what this self-development stuff has to do with style, fashion and image?

It’s because making a decision between one of those paths is the quintessential quality of reaching the stage three of image mastery – being a well-dressed man.

Your Well-Dressed Man

All three outfits are quite well executed, but it’s the mindset behind them that makes them Stage Three and in situations where they did connect with my type of women, it was blind luck first, skill second

Being well-dressed can be summed up with two qualities:

The outfit is well-executed in terms of colors, patterns, cuts and styles.

The outfit is appropriate for a venue or occasion.

Yeah, it’s that (relatively) simple.

So when your typical (not so) Average Joe gets a firm grasp of the fundamentals and moves to the next stage of the image mastery journey – he’s now a well-dressed man.

At this point two things happen:

First, you notice that the feedback you’re getting about your looks and image is positive and consistent: you get complimented on your clothes regularly and get called “handsome/stylish”, you occasionally catch women checking you out and in general finally clothes are working to help you with your romantic goals, not against them.

However, once the novelty of the new-found attention wears off, you notice the second thing:

That all this positive feedback doesn’t necessarily translate into better results with women, as in making it notably easier to meet them, date them and bed them. On the same note, you notice that whenever you go out there are quite a few other guys who are dressed in a closely similar fashion.

Unsurprisingly, at this point it’s easy to start thinking “pfff… so that’s it? A few compliments here and there? Not being shot down the moment you say “Hi!”? A few more matches on Tinder? That’s the best being well-dressed man has to offer?”

At this point you will need to make the decision that we talked about earlier in the article:

Are you going to call “bullshit!”, quit and get back to wearing cargo shorts, sandals and oversized band t-shirts?

Are you going to stick with what you’ve learned, but instead of learning how you can improve and refine your skills, you put this whole endeavor on hold and focus maybe on improving your physique, increasing your income or becoming a better conversationalist?

Or will you get excited with what you’ve learned so far, the improvements with women you’ve seen so far, and decide you want to see how far you can push this? Will you see what’s behind the closed curtains of Stage 4 and 5 (or maybe even further…)?

Unfortunately, very few men actually choose the latter option and instead you see guys on reddit, forums, etc. complain how they all “dress very well, but it doesn’t seem to make much of a difference.”

The reason here is that even though we can essentially sum up what being well-dressed means in two points like we did above, to truly grasp what it means to be a well-dressed man in the big picture of image mastery, we also need to include two points that it LACKS:

Well-dressed men are not polarizing – because most guys at this stage try to follow fashion rules with an almost religious zealousness, they have very little edginess or raw sex appeal to them. In most cases they are stylish, but rather nice. Even the edgy / elegant-edgy looks are quite mild and restrained.

Well-dressed men think in outfits, not image – even though a well-dressed guy can easily tell you what items go well together in an outfit or how to coordinate colors, if you asked him what kind of image he is going for, what qualities he wants to communicate, or who’s his “audience” (the type of women he wants to attract)? He’ll just stare at you dumbfounded, “what do you mean?”

In other words, what most well-dressed men do is they put together something thats actually nice and well-executed, but miss the deeper aspects of image required of more ambitious goals, so when they walk out into the world they find themselves coming up short despite “doing a good job.”

Common Mindsets Among Well-Dressed Men

“My outfits are well put together, what else do you want?!”

Well-dressed men tend to be obsessed with polishing the rough edges, smoothing everything out. They don’t yet see that the edges, the imperfections that make us unique and interesting, are valuable assets that can be mastered.

So when they go out and realize that their image is appealing to everyone, but captivating to no one, they start looking for some other X factor to explain the success of someone who purposefully and stylishly breaks the rules of being well-dressed: “oh he must be rich”, “he must have mad game”, etc.

And hey, maybe his rationalizations are correct, but it simply doesn’t matter when it comes to your progress and success.

In style and fashion, it’s when you start breaking the patterns, the expectations, and purposefully introduce imperfections that polarization and sex appeal can manifest itself in the chaos.

“My outfits need to be appropriate for the situation at all costs…”

This is another big obsession of a typical well-dressed man – looking appropriate. It’s not surprising to find these guys spending hours on the internet, reddit and fashion forums looking for an answer to the elusive question “how do I dress for …?”

In the mind of a well-dressed man, individuality and personal preferences is but an echo in the background compared to the overwhelming need of looking appropriate.

To achieve this, a typical well-dressed man will gladly sacrifice sex appeal or character just as long as his outfits are deemed fitting by everyone else.

By the way, when I say “appropriateness” I don’t just mean formal events and job interviews, but also any social situations that include certain fashion-aware social circles, i.e. teens spending money they don’t have on popular brand sneakers and hoodies just so they fit in a particular sub-culture.

They think they are being cool and edgy, when in reality they just follow trends set by someone else in that culture in the hopes of being deemed appropriate by their peers.

“If numerous people dislike my outfits/style, then it sucks…”

Given the first two mindsets we discussed, it shouldn’t be a surprise that a concept like polarization is completely out of touch with a well-dressed man’s reality.

Polarization means that instead of trying to look appealing to everyone and fucking hot to no one, we instead switch gears and focus on looking fucking hot to the type of women that we are attracted to the most, even if others might not necessarily approve or like our image.

For a well-dressed man if numerous people claim that they are not a fan of a look, it won’t matter that there are some who absolutely love it, because it’s the negative feedback that he will focus on.

“XZY style is going to be popular this season, therefore I should build my outfits around it…”

In the quest of appropriateness, most well-dressed men choose one of two strategies.

The first group becomes obsessed with fashion brands and trends. They love reading articles like “8 Big Menswear Trends That Will Be Popular Next Season” and follow their favorite brands religiously.

These are the guys, whose image for the season depends on what big fashion brand houses decide to push.

These are also the guys that you can see waiting in line for hours when some overhyped brand is about to launch its new product line.

There’s nothing wrong with being fashion aware and making adjustments to your outfits as trends change, nor is there anything wrong with having a favorite brand or paying premium for high quality products.

It’s when being fashion-forward or hip takes priority over creating an image that reflects how you want to present yourself to the world and attracting your ideal type of people into your life, that we have a problem and a bunch of men stuck in stage three of image mastery.

“It’s all about the classic styles…”

The second group discards fashion trends altogether and for them its all about classic, always-in-fashion styles and outfits.

These well-dressed men find a lot of comfort in knowing that their “appropriateness” is grounded on tradition and etiquette. They appreciate that instead of figuring out the image they want to create they can essentially outsource the decision on how they should dress to various rules, norms and best practices.

Once again, there’s nothing wrong with preferring classic, traditional styles as long as they are not too dumbed down to the point of having no sex appeal whatsoever. After all, the Sharp image is one of my personal favorites too (right after Elegant – Edgy).

But if we want to move further towards the next stage of image mastery, we need take control over the image we want for ourselves, instead of relying solely on traditions, norms and etiquette.

“ZXY celebrity is now wearing this style, therefore I should go for a similar look too…”

Not having a strong understanding of the image we want to go for means that we will need to resort to looking for style inspiration externally, and celebrities and fictional TV/movie characters tend to be popular sources for that.

Several years ago it was all about Johnny Depp and David Beckham, these days its more about Kanye West and Justin Bieber (oh, how I miss the good old days…).

The point is that even though modeling (aka borrowing ideas) is a valuable tool in a sexy man’s toolbox, to get better and move to the next stage of image mastery we need learn how to find the perfect image for us first, and then we can look into celebrities who embody this image for specific ideas.

Biggest Mistakes & Pitfalls

A well-dressed man is someone who managed to overcome the most treacherous first steps of image mastery while correcting any pitfalls and big mistakes along the way, but that’s not to say that there’s no danger ahead of him and knowing the common mindsets among these men, we can now better understand the mistakes they make:

Becoming a fashion technician – a “fashion technician” is a well-dressed man who’s obsessed with the details instead of focusing on their image, and as a result they become experts on fabrics, cuts, and techniques while their own image doesn’t improve in the process. Becoming a master fashion technician is necessary if you want to become a craftsman, maybe a designer, but when it comes to simply looking our best, it’s a secondary and optional skill, at least while one is in this stage.

Obsession with brands – having favorite brands is great: it makes shopping easier, you can find novel and interesting items to experiment with, and clothes from the same brand are generally easier to combine in an outfit. However, it’s important to remember that our image should dictate our selection of favorite clothing brands, and NOT vice versa. You can find good looking clothes from cheap fast fashion brands, and you can also find absolute piles of crap with a very expensive price tag from luxury brands. On top of that, paying premium just to have a certain logo/brand name on your clothing is straight up stupid. Paying premium for real quality, now that’s another story.

Disillusionment and giving up – but the biggest mistake and potential pitfall the well-dressed man faces is getting discouraged and giving up on being a well-dressed man. Reverting to a (not so) Average Joe, or worse, The Basement Dweller. It’s like watching someone who has developed a pretty solid physique over months and years, then do a 180 and get obese.

Typical Reactions Well-Dressed Men Get

Now, we’ve been pretty hard on this stage, but only for the sake of mastery. Its definitely not all bad.

Let’s look at how being a well-dressed man simply makes everything easier and more enjoyable:

In private conversations between women you will often be referred to as cute, handsome, attractive or something similar.

You will notice women checking you out rather regularly and you will get complimented on your clothes and/or style.

If your photos are not complete crap and you don’t live in the middle of nowhere, you should have enough matches on Tinder to keep yourself busy, at least for the texting part.

Women will be more receptive to your approaches when you meet them during the day and/or at night.

In general you will notice that people are more receptive, nicer and treat you with more respect.

On top of that, if you have solid game, an impressive physique, or are naturally handsome, getting to this stage of image mastery can be just enough of a push to start snowballing the results you get in your romantic life.

(Quick note: if you’re way behind in terms of game, physique and/or natural looks, you should still notice the benefits of being a well-dressed man, just to a lesser degree)

What you are unlikely to notice, is women going out of their way (sometimes even literally) to meet you or make something happen with you.

Overall, it is a good stage to be in, especially if you have other things going for you too.

And in all honesty, I do think that’s a good spot to take a breather and work on some other skills or projects.

Then, when you’re ready, it’s time to move to stage four of image mastery.

How To Get To The Next Stage

And now its time to discuss practical and actionable steps you can take to move beyond being a well-dressed man:

Define your perfect image and start experimenting – a “perfect image” happens where lifestyle suitability, personal preferences and what gets you results meet. Results include accurately communicating specifically chosen characteristics with your image and attracting the type of people you want into your life.
If you want to get to stage four of image mastery, this is the first thing you need to tackle, you need to know what you want to communicate with your image and the type of people you want to attract into your life. This will give you insight into the tweaks you’ll be making for improved results.

Start thinking in image, not just outfits – until this point we could get away with looking at the way we dress from a very technical, algorithmic point of view: Color X works with color Y, but doesn’t work with color Z, therefore I should wear X blazer with Y jeans; a biker leather jacket works well with boots and converse, but is very difficult to pull off with loafers, therefore when wearing biker leather jackets I should only choose between boots or converse. To get past the stage of a well-dressed man, you need to be able to move beyond this linear and structured thinking. Instead, before even considering the outfit, we start with the type of image we want to create, the qualities we want to communicate about ourselves, and from there, we can build an outfit. Interestingly, you might find yourself breaking some of the rules that in the past you considered sacred.

Adjust your hairstyle and facial hair style based on the image you want to create – this is probably the least impactful thing to do/consider, but because I know so many guys are looking for a flattering and suitable hairstyle and facial hair style, it makes sense to include how it translates when going from stage three of image mastery to stage four. Just like clothes, your hairstyle and facial hair have inherent associations with them and communicate something about you. The simplest example to illustrate this are beards – not pretty or handsome, but rugged, masculine and potentially very sexy to women. So as you’re becoming a sexy man in the making and know the image you want to go for, you can use these inherent qualities to your advantage. For example, if you prefer the classic, dressy outfits such as Smart – Casual or Sharp, but decide that you’re better off with a more masculine, edgier image overall, you can grow out your facial hair and choose a hairstyle that’s a bit more waywardish and/or hip (let’s say the man bun). On the other hand, if you’re rocking an edgy or rugged-masculine image but don’t want to come across as too aggressive or intimidating, you can clean shave and pick a neat, classic hairstyle.

Recommended reading – I don’t have an article that goes in depth on how different hairstyles and facial hairstyles fall into various image spectrums but I have touched on it in the Sexy Man’s Grooming Guide, Part 3: Choosing a Hairstyle article, last section “Your Full Image”. If there’s interest I might write a full piece on the topic (but you’ll have to let me know )

As you can see, moving from stage three to stage four is more about the mindset, the thought process behind how and why we dress the way we do, instead of just trying to improve our “technical” dressing skills.

Also, we’re not yet touching polarization directly. Instead, as you start focusing more on your image and less on outfits themselves, you should notice that the way you dress becomes a bit more polarizing naturally and you just need to avoid interfering or trying to restrain yourself.

Finishing Thoughts

To finish this part of the series, I’d like to say that I genuinely like stage three of image mastery and some of my fondest memories are from those days, though at the time I didn’t realize I would one day refer to myself as “well-dressed,” heh. I think its fair to say that I was in this stage of image mastery when I started Sexy Style for Joe.

If you find yourself at this point, don’t take it for granted and enjoy the ride.

Because when we go from stage three to stage four, the world gets quite a bit crazier again as we start experimenting with image as a whole and start experiencing the wild ride that is polarization.